Men who are laid back in dating/relationships. Do you prefer a more assertive woman?

I have a guy friend who is having self proclaimed issues with dating. He wants to meet someone and settle down, as he's 44 and doesn't have any children. He is however VERY laid back when it comes to pursuing women. He's attractive, fit, very smart and makes excellent money. However, every time he meets a decent woman, I think she gets bored with him, or interprets his approach as disinterest. I told him to try dating women that are maybe a little more proactive ( they make the first move, plan dates, initiate the communication) but he said those women tend to be masculine/aggressive and he prefers a softer type. Sigh. If this was your homeboy, what advice would you give him? He's always been this way apparently and has had a few long term relationships. But he's been single now for a few years and has only had flings since then.